Man onboard UP Express train working on this laptop

The Digital Nomad Handbook: Perfecting Remote Work & Travel

Published: October 20, 2023

With employers offering remote work for more flexibility, people are increasingly living the Digital Nomad lifestyle. So, what does this mean, exactly? This blog will explain what a Digital Nomad is, what you need to become one, and if it is a good fit for you and your lifestyle! Get tips on how to be a Digital Nomad, ideal places to work from, and some best practices on how to maximize your experience and protect yourself and your travelling workspace. Learn what work looks like in other countries, but If you’re staying in Toronto or coming in to be a Digital Nomad in the GTA, UP Express is the stress-free and convenient way to travel from Pearson Airport to downtown Toronto!

Person standing at the top of a viewpoint with laptop in hand

What is a Digital Nomad?

A Digital Nomad is someone who works remotely, using the internet and other technologies to do their job while simultaneously travelling. With the COVID-19 pandemic changing the work structure for many employees around the world, many embraced remote work and realized how they could do the same job outside of the office. Employees also learned that the Digital Nomad lifestyle worked for them, with many going out on their own in the gig economy, using the skills that they had built in the office environment, and transferring those skills to working from home.

Because of their remote nature and frequent changes of location, Digital Nomads do not have many material possessions. Many of these workers are programmers, content creators, freelancers, writers and editors, graphic designers, photographers, coders, or developers. Their places of work could include cafés, hotels, temporary housing, hostels, libraries, or even their vehicle.

Can you be a Digital Nomad?

Do you want the flexibility to set your own schedule? Digital Nomads can work any time and anywhere. You might be considering becoming a Digital Nomad to enjoy a better work/life balance, remove the work commute and office distractions, and try a different type of job market. But would you be a good fit for this lifestyle? First, you can’t be a digital nomad if you’re averse to change. Your location is consistently changing, and you don’t necessarily have a home. And if you do have a home, it’s not for a long period of time. Digital Nomads typically spend a few months away from their home country at any one time and change their locations anywhere from every few weeks to half of the year.

Do you adapt well to changing situations such as your location of work and living? Can you troubleshoot if you run into technical challenges? Are you technologically savvy? You’ll have to be all of these if you want to be a Digital Nomad for any longer stretch of time.

What You'll Need to Be a Digital Nomad

Before you embrace Digital Nomadism, you must know what’s involved. Do you have the skills necessary to make this a viable option? If you’re unsure, you might want to consider upgrading key skills in content and/or digital marketing, blogging and other content creation, web design, writing, and other language skills. If you don’t have a main employer, you’ll have to sharpen your skills so that you have much to offer prospective clients.

Networking skills will also be important in order to gain business and income if you’re freelancing. You may have to sign up for some gig economy websites, such as Upwork,, or Fiverr to build your reputation and your client base. It may also be important to take classes online that will help you understand how your work situation will change and how to best manage your time and your work/life balance.

Additionally, as you begin your journey to become a Digital Nomad, you’ll want to minimize your possessions and your expenses. That could involve selling large items or putting them in storage. Review your subscriptions, your memberships, and any other regular payments that you’re making. Will you still need them when you begin this new lifestyle?

Other options that might be more appealing, especially when you’re getting started, are finding anyone who needs their house to be watched while they’re away, or possibly watching a dog or another pet at someone else’s home. These options could be good ways to discover if the lifestyle is for you.

Living in Toronto as a Digital Nomad

Man onboard UP Express train working on this laptop

If you’re deciding on making Toronto your home base to be a Digital Nomad, where should you go? We have extensive neighbourhood guides that will help you choose the best fit for your lifestyle and preferred work environment. Remember that UP Express can get you to downtown in 25 minutes from Pearson Airport!

Toronto is a popular destination because of its diversity. Different neighbourhoods have different cultural influences, so you’ll be able to find a fit for both your preferred working environment and lifestyle somewhere in the region! If you’re looking for a full breakdown of how Toronto ranks for different Digital Nomad preferences, the nomadlist has it for you.

How to Decide Where to Go

Person scrolling on phone at desk with laptop open

Start by making a list of places that you’ve always wanted to visit, places that you’ve been to, and where you would consider living. Then, ask yourself these questions:

  • Does the cost of living work with your budget?
    • Housing
    • Transportation – Did You Know? UP Express is North America’s first dedicated air-rail link providing a 3km rail service connecting Toronto Pearson Airport direct to downtown Toronto. Then there’s GO Transit, the inter-regional bus and rail service linking Toronto with outlying areas of the Greater Golden Horseshoe. TTC is the city’s local transit system offering subway, bus, and streetcar service to millions of inter-city passengers. If you are travelling on the TTC, you can easily connect to UP Express and GO Transit stations. All of these and more transit options across the region with PRESTO. When you arrive in Toronto, you can purchase your PRESTO card online via, in-person at an UP Express or GO Transit stations, or the nearest Shoppers Drug Mart in your area. You can load and check funds on your PRESTO card from the PRESTO App, in person from a Ticket Vending Machines at an UP or GO stations, or at these Customer Service outlets. UP Express, GO Transit, TTC, and other transit agencies across the GTHA accept contactless payment allowing riders to use their debit card, credit card, or mobile wallet on phone or watch to pay for your fare. For more information about contactless payment, visit Remember to tap on your PRESTO card or contactless payment on a PRESTO device before boarding an UP or GO train, GO bus, or entering a TTC station to connect to a local subway or bus. And don’t forget to tap off before leaving an UP or GO station at your end destination. It’s that easy!
    • Access to Internet/Wi-Fi; Is there good infrastructure for what you want to do? When you’re on UP Express, connect to the free Wi-Fi in the station, onboard, and even on the platform!
    • When you’re on the go and don’t want to have to rely on public Wi-Fi, which can be slower and potentially not secure, purchase a Mobile Wi-Fi Hotspot to stay connected while you’re on the go! There are 3 types of Mobile Wi-Fi Hotspots ideal for remote work and international travel:
      1. Mobile Wi-Fi Hotspots – these are pocket-sized gadgets that can automatically connect you to a cellular network and create a Wi-Fi network for your devices.
      2. Portable Wi-Fi Routers – offers extra perks like Ethernet ports and external antenna support but you may need a separate USB port, modem, or SIM card
      3. USB Modems – these are little devices that plug directly into your laptop or computer giving you a personal internet connection. Remember, they are usually tied to a Wi-Fi connection from a specific carrier and require a separate data plan.
    • Costs of Mobile Wi-Fi Hotspots range from around $60 to $200, depending on what you’re looking for. Here are some of the top options:
  • Did you know? The Canadian government just announced a Digital Nomad visa that will allow Digital Nomads in tech roles to stay up to six months with their visitor visa.
  • What is the cost of Travel Insurance? There are a variety of options out there, and costs vary depending on what type of coverage you want, how long you’re travelling for, and which destinations you are choosing. To get started, some of the top travel insurance companies include Blue Cross, CAA, and Manulife’s CoverMe.
  • If you have a stable employer(s), would the time zone change (if applicable) work for your deadlines, meetings, and your supervisor?

Once you’ve curated a list and then narrowed it down, start thinking about what kind of city or neighbourhood you prefer to live and work in. Is it a diverse city? In order to help get the most out of your experience, you’ll want to embrace diversity and the local culture. What places would you like to see or events would you want to take part in?

Digital Nomad Housing

Since where you live is probably the biggest factor for a successful work environment and experience, we’ll delve deeper.

  • Co-ops or hostels: If you want to meet new people, share resources, or learn from others who are doing what you’re doing, this is a good option.
  • If you prefer privacy and working in the quiet, then an apartment, a long-term hotel stay, house-sitting or other separate rental space are better ideas.
  • Digital Nomad Hubs, such as the Noma Collective, are similar to hostels or co-ops but in this case, you’re working among your peers and a community. Together, you pool the accommodation costs and also learn from each other. These setups are becoming more and more popular as the typical work environment continues to evolve. And who knows? You might meet someone and travel together to your next destination.

Not everyone who chooses this lifestyle will be able to live and work just anywhere. You’ll need access to a stable Wi-Fi connection, affordable, safe, and comfortable housing, and food that fits your preferences and budget. So where are the popular destinations for Digital Nomads? After curating lists from a handful of Digital Nomad resources, we found the following cities to be popular across the board:

Woman sitting in lounge chair with laptop in front of viewpoint
  1. Lisbon, Portugal – Incredible value for money for accommodation and living expenses, including internet access. Rich culture, beautiful beaches, great views from this hill-top city, and an underrated restaurant scene.
  2. Melbourne, Australia – Decent cost of living, excellent internet access and speed, and popular with students, tourists, and expats. There are plenty of cafés, and Melbourne has a rich cultural scene.
  3. Austin, Texas – You’ll pay more to live in Austin, but you won’t find another popular Digital Nomad city with better internet access or speeds. There is also plenty of culture, arts, and music to enjoy. It’s a top choice if you want to stay in North America.
  4. Chiang Mai, Thailand – A great value for the cost of living, good internet speeds, abundant corking spaces, a busy night market, stunning temples, and a nearby jungle.
  5. Canggu, Bali, Indonesia – Plenty of coworking spaces, a great beach vibe, and solid internet speed. Transportation infrastructure can be an issue, however.
  6. Budapest, Hungary – A decent cost of living, some of the best internet speeds available; great dining, and a beautiful old city charm on the Danube River.
  7. Medellín, Colombia – One of the most popular cities in South America for tourists, expats, and Digital Nomads, the city has a strong vibe, a great climate, and lush surroundings. Enjoy a top-class dining experience, nightlife, and most importantly, a plethora of coworking spaces. Medellín also has a great metro system, Uber, a good cost of living, and quick internet speeds.
  8. Tulum, Mexico – Pricier on the cost of living, Tulum has fast internet speeds, beautiful water, and is situated in a great spot for travelling to other areas of Mexico and the United States. There is plenty to explore, with Mayan ruins and other historical sites to see, and all within bicycling distance! There is also a strong culinary scene, and coworking and co-living spaces. 
  9. Ho Chi Minh City, Vietnam – Reasonable cost of living, good internet access and speed, a fast pace of living with a good nightlife, and incredible cuisine. There are also plenty of young, creative workers who call Vietnam’s biggest city home.
  10. Cape Town, South Africa – A big city surrounded by mountains, incredible nature, beautiful beaches, plenty of coworking spaces, a vibrant cultural scene, and a reasonable cost of living.
  11. Berlin, Germany – A little more expensive cost of living, but Berlin is a city with big-time energy, creative and artistic culture, quick internet speeds, and plenty of history to learn.
  12. Barcelona, Spain – A popular destination that lends to a higher cost of living, but you’ll likely stay longer because of its beauty, beaches, infrastructure, and green areas. Digital Nomads have made this a hub with countless coworking spaces and groups.

What Else You Need to Know About Digital Nomadism

It’s important to have all of your key documents and account information backed up should you unfortunately lose any of them during your travels, especially if you are in another country. This could mean having a photocopy or taking a photo of your documents and storing them on your phone or on a cloud-based app. Here are some examples:

  • Passport
  • Driver’s License
  • Birth Certificate
  • Banking Information
  • Doctor’s Notes
  • Prescription information

Make A Plan

While things can change once you’re out and experiencing the life of being a Digital Nomad, setting goals and formulating a plan before you go is a good idea. List the destinations that you want to visit, and how long you want to stay. Also include what your goals are, and what you do if you run into any issues along the way. These could be unforeseen changes at your destination, weather challenges, trouble getting around, or health concerns. You’ll also have to evaluate your productivity and ability to adapt to these changing situations and environments.

Digital Nomad Best Practices

Woman sitting at desk working on laptop

Becoming a Digital Nomad is a massive change. So, what can you do to give yourself a better chance at success? We have ten tips for you:

  1. Establish a Routine – Create a list of your daily tasks, and what you need to do and by when. If you prefer meetings in the afternoon, keep a block of time in the afternoon for them. Social media management in the morning? Keep that as part of your daily tasks. When do you complete your best work? Doing the same work-related tasks at the same time gives you a better chance of completing them, staying on top of your work, and building your brand.
  2. Don’t Forget Your Breaks – When you are working for yourself, you may forget that you still need to take your breaks, especially if you’re at a desk or sitting down most of your day. Standing up, walking around, and getting outside can help energize you, give your eyes a break, and perhaps spark your creative side!
  3. Clocking Out – As with your breaks, set a time when your workday ends and include that in your routine and schedule. It might be tempting to get another task done, but having work bleed into your leisure time can start a trend. Before you know it, you’ll frequently be working past your set time.
  4. Keep Up Your Hobbies – While you might be in a different location or country, you should still do what you love. Keep up with your working out, your reading, exploring the country and city, or whatever else you love to do!
  5. Stay in Touch – Scheduling regular time with your family and friends can help you feel connected to your home, reduce loneliness, and energize you!
  6. Set up Your Workspace – Wherever you are located as a Digital Nomad, creating a designated workspace is important. It separates you from distractions and keeps you focused on your work. Avoid setting up your workspace with the TV in your sightline. And will a desk by a window help or hinder you? It might provide inspiration, or it might distract you from your work. If you’re working elsewhere in the city, where do you get your best work done? At a busy café? Or a quiet library or coworking space?
  7. Look the Part – It may be tempting to work in the most comfortable of clothes, but that may not entice a working mood and feeling. Work time should feel like work time. And what if you get an impromptu video call?
  8. Feed Yourself – Sometimes you can get on a roll and be very productive. But, don’t forget that you need to keep your energy level and motivation high. Ensure you have a water bottle to drink from and have scheduled your meal times.
  9. Technology – Don’t cut corners when you’re dealing with the technology that connects you with your clients, and ultimately helps to earn you a living. Make sure that your laptop has memory and speed capabilities that are on the higher end. Also, purchasing a VPN and security software will prevent data breaches and reduce the chances of a virus ruining a laptop, leading to lost work and earnings. If you’re working from your home base, set yourself up for success by buying an ergonomic chair, a good keyboard, and maybe some headphones to block out noise and distractions, or help motivate you with some good music.
  10. Other Rules – If you’re in a co-working space or living with others, arrange some ground rules with your co-habitants. What times would you prefer quiet time for your work? What time do you need to use the kitchen or do laundry?

Becoming a Digital Nomad can be an exciting time! If you’re looking for a change in your life and want to visit new places, it’s certainly a good option. Or perhaps you want more purchasing power in places with a lower cost of living. This lifestyle could afford you a better place to live, the ability to engage in more recreational activities, and a better work environment and style for you. You’ll also likely learn a lot from others to improve your skills, build your brand, and find what works best while learning more about yourself!

And if you’re staying in Toronto, UP Express is one of the many convenient modes of transit to use. It’s only 25 minutes to downtown from YYZ, and trains run every 15 minutes! So, load up the PRESTO card and find your workplace!